This thesis presents an in-depth, idiographic analysis of the lived experiences and perceptions of women deputy headteachers: a relatively under-researched professional group. The study aimed to explore the ways in which twelve women deputy headteachers, as potential aspirants to headship, perceived the secondary headteacher role. Given the persistent under-representation of women in secondary headship, it sought to investigate participants’ career histories and how these had informed their professional aspirations. Semi-structured interviews were conducted with twelve participants. All interview transcripts were analysed using Interpretative Phenomenological Analysis (IPA). Three super-ordinate themes emerged from the data: ‘managing constraint’, ‘motivating forces’ and ‘perceptions of secondary headship and the future’. Detailing different aspects of the deputies’ experiences, the themes highlighted the complexity of the women’s impressions of secondary headship, the heterogeneity among potential headteacher aspirants and the importance of critical reflection while deciding one’s professional future. Drawing on Margaret Archer’s theory of reflexivity as a mediatory mechanism between structural forces and human agency, this thesis proposes three types of potential headteacher aspirant: ‘the strategic and decisive leader’, ‘the values-oriented professional’ and ‘the person-centred educator’. These ideal types illustrate the heterogeneous ways in which a small sample of women deputies had reflected on, positioned themselves towards and navigated their way through their careers in secondary education. This typology together with the nuanced analysis advanced throughout this thesis offers a unique contribution to knowledge. Various implications for practice and research are discussed. I conclude by arguing that the under-representation of women in secondary headship is a complex phenomenon, and that the career narratives of individual potential aspirants deserve a place at the heart of our theorising and understanding of it. The findings reported in this thesis may be of interest to potential headteacher aspirants as well as those tasked with identifying and training tomorrow’s leaders.